{"data":{"id":"10.6084/m9.figshare.785753","type":"dois","attributes":{"doi":"10.6084/m9.figshare.785753","prefix":"10.6084","suffix":"m9.figshare.785753","identifiers":[],"alternateIdentifiers":[],"creators":[{"name":"Clarke, James","nameType":"Personal","givenName":"James","familyName":"Clarke","affiliation":[],"nameIdentifiers":[]},{"name":"Rzepa, Henry S.","nameType":"Personal","givenName":"Henry S.","familyName":"Rzepa","affiliation":[],"nameIdentifiers":[{"schemeUri":"https://orcid.org","nameIdentifier":"https://orcid.org/0000-0002-8635-8390","nameIdentifierScheme":"ORCID"}]},{"name":"Braddock, D. Christopher","nameType":"Personal","givenName":"D. Christopher","familyName":"Braddock","affiliation":[],"nameIdentifiers":[{"schemeUri":"https://orcid.org","nameIdentifier":"https://orcid.org/0000-0002-4161-7256","nameIdentifierScheme":"ORCID"}]}],"titles":[{"title":"(E-2-13C)-Non-2-enoic acid"}],"publisher":"figshare","container":{},"publicationYear":2013,"subjects":[{"subject":"Organic Chemistry"},{"subject":"FOS: Chemical sciences","schemeUri":"http://www.oecd.org/science/inno/38235147.pdf","subjectScheme":"Fields of Science and Technology (FOS)"},{"subject":"FOS: Chemical sciences","subjectScheme":"Fields of Science and Technology (FOS)"}],"contributors":[],"dates":[{"date":"2013-09-02","dateType":"Created"},{"date":"2013-09-02","dateType":"Updated"},{"date":"2013","dateType":"Issued"}],"language":null,"types":{"ris":"DATA","bibtex":"misc","citeproc":"dataset","schemaOrg":"Dataset","resourceType":"Dataset","resourceTypeGeneral":"Dataset"},"relatedIdentifiers":[],"relatedItems":[],"sizes":["377010 Bytes"],"formats":[],"version":null,"rightsList":[{"rights":"Creative Commons Attribution 4.0 International","rightsUri":"https://creativecommons.org/licenses/by/4.0/legalcode","schemeUri":"https://spdx.org/licenses/","rightsIdentifier":"cc-by-4.0","rightsIdentifierScheme":"SPDX"}],"descriptions":[{"description":"To a stirred solution of either (1-13C)-1-bromonona-1,2-diene [(1-13C)-4] (100 mg, 0.49 mmol) in acetone (2 mL) at -40 °C was added a 0.10 M solution of DMDO in acetone (3.20 mL, 0.320 mmol). The colourless solution was warmed to room temperature and stirred overnight. The solvent was removed in vacuo and the residue extracted with Et2O (3 × 2 mL) and petroleum ether (3 × 2 mL). The combined organics were evaporated to give a yellow oil (104 mg). Column chromatography (petroleum ether : EtOAc 4 : 1 to 1 : 2) gave (E-2-13C)-5 (10 mg, 0.064 mmol, 14%, 96% 13C-2, 4% 13C-1 atom) and (Z-2-13C)-5 10 mg, 0.064 mmol, 14%, 96% 13C-2, 4% 13C-1 atom) as colourless oils [the 13C content at the 1- and 2-positions were deduced by inspection of their 1H NMR and 13C NMR spectra (see ESI p44-45)]. (E-2-13C)-5: Rf 0.14 (petroleum ether : EtOAc 6 : 1); IR (neat) 3300-2800, 1692, 1627 cm-1; 1H NMR (400 MHz, CDCl3) δ 7.06 (ddt, J = 15.6, 7.0, 1.8 Hz, 1H, β-H), 5.78 (ddt, 1JCH = 163, J = 15.6, 1.5 Hz, 1H, -H), 2.21 (ddq, J = 6.8, 6.0, 1.5 Hz, 2H, CH2CH=13CH), 1.48 – 1.40 (m, 2H, CH2), 1.32 – 1.22 (m, 6H, 3 × CH2), 0.87 (t, J = 7.0 Hz, 3H, CH3); 13C NMR (101 MHz, CDCl3) δ 170.8 (d, J = 74.2 Hz, CO2H), 152.4 (d, 1JCC = 69.7 Hz, β-C), 120.3 (-13C), 32.3 (CH2), 31.6 (CH2), 28.8 (CH2), 27.8 (CH2), 22.5 (CH2), 14.1 (CH3); MS (CI+, NH3) m/z 175 (M + NH4)+; HRMS (CI+, NH3) m/z calcd for C8(13C)H22NO2 (M + NH4)+ 175.1527, found 175.1527.","descriptionType":"Abstract"}],"geoLocations":[],"fundingReferences":[],"xml":"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","url":"https://figshare.com/articles/dataset/_E_2_13C_Non_2_enoic_acid_/785753","contentUrl":null,"metadataVersion":2,"schemaVersion":"http://datacite.org/schema/kernel-4","source":"mds","isActive":true,"state":"findable","reason":null,"viewCount":0,"viewsOverTime":[],"downloadCount":0,"downloadsOverTime":[],"referenceCount":0,"citationCount":0,"citationsOverTime":[],"partCount":0,"partOfCount":0,"versionCount":0,"versionOfCount":0,"created":"2013-09-02T18:44:07.000Z","registered":"2013-09-02T18:44:08.000Z","published":"2013","updated":"2020-09-05T01:31:20.000Z"},"relationships":{"client":{"data":{"id":"figshare.ars","type":"clients"}},"provider":{"data":{"id":"otjm","type":"providers"}},"media":{"data":{"id":"10.6084/m9.figshare.785753","type":"media"}},"references":{"data":[]},"citations":{"data":[]},"parts":{"data":[]},"partOf":{"data":[]},"versions":{"data":[]},"versionOf":{"data":[]}}}}